Britney Spears’s Leonardo DiCaprio #tbt Brings the 90s Roaring Back to Life

Britney Spears at the 2005 premiere of Charlie and the Chocolate Factory.

Left, from NBC, right, by Dimitrios Kambouris, both from Getty Images.

Take yourself back to early 1999. A time of Y2K fear, economic expansion we thought would never end, television domination by people named Frasier and Dr. Carol Hathaway, and two stars whose first names were enough to cause a stampede: Britney and Leo. By 1999 Titanic had been in theaters for over a year, its Oscar domination had come and gone, but Leonardo DiCaprio remained a cultural phenomenon, inspiring scores of teenagers to build their first Geocities tribute pages and an entire industry to pin their hopes on Leo as the next big thing. And meanwhile, over in the music industry, a 17-year-old named Britney Spears arrived in January of 1999 with an album and, more importantly, a music video that played off every imaginable horny fantasy of Catholic schoolgirls. It was a pop culture atom bomb nearly as big as Titanic; as Leo spent 1999 filming The Beach and planning his next movie, Britney took the world all for herself.

Now, stay in that 1999 headspace and imagine this: Britney and Leo, hanging out. Could the world have ever survived it? Can you even survive the idea of it today, after this #tbt post from Miss Spears yesterday? Take a deep breath and give it a try.

Before you go revise your Britney-Leo fan fiction from the last millennium, it’s worth noting that this photo is probably not from their respective heights of 1999—both look a bit older, for one thing, and Leo’s Red Sox cap suggests this could be from around 2005-2006, during the filming and release of The Departed. At the time Brit was nearing the end of her marriage to Kevin Federline, expecting her second son, and under the intense media scrutiny that eventually led to the famous 2007 “meltdown.” Leo won a Golden Globe for The Aviator, attended the 2005 Oscars with Gisele Bundchen, and worked with Scorsese again on The Departed—pretty much par for his course. So how did the two cross paths around this time? What did they talk about other than how crazy it was that it had been five full year since the 90s ended? Britney’s cryptic, minimalist caption tells us nothing.

So just enjoy this photo for what it is—a surprising blast from the past that inspires far more questions than it answers, and that proves that maybe everything that happened in the late 90s really is connected. Any chance Ricky Martin is somehow cropped out of this photo?

Photos: Leonardo DiCaprio, Ryan Gosling, Terrence Howard, and More Before They Were Stars

LEONARDO DICAPRIO, MARCH 1995

BREAKTHROUGH ROLE: Toby in This Boy’s Life.CAREER HIGHLIGHTS: Jack in Titanic—at age 23. Oscar-nominated for The Revenant (2015), The Wolf of Wall Street (2013), Blood Diamond (2006), The Aviator (2004), What’s Eating Gilbert Grape (1993). WHAT HE SAID THEN: “I can’t stand movies about reality that don’t deal with that reality.”

Photo: Photograph by Michael Roberts.

CHANNING TATUM, APRIL 2009

BREAKTHROUGH ROLE: Tyler Gage in Step Up.CAREER HIGHLIGHTS:Foxcatcher, Magic Mike, 21 and 22 Jump Street.WHAT HE SAID THEN: “I got introduced to the whole modeling thing and then I did a Pepsi commercial. That was a lot more interesting to me than just standing in front of a camera with some clothes on.”

Photo: Photograph by Norman Jean Roy.

VIN DIESEL, APRIL 1999

BREAKTHROUGH ROLE: Private Caparzo in Saving Private Ryan.CAREER HIGHLIGHTS:Fast & Furious franchise. WHAT HE SAID THEN: “When I was seven ... buddies and I vandalized this theater. The lady caught us and said, ‘Come here every day after school. I’ll pay you $20 a week.’ ”

Photo: Photograph by Mike Ruiz.

RUSSELL CROWE, SEPTEMBER 1997

BREAKTHROUGH ROLE: Bud White in L.A. Confidential.CAREER HIGHLIGHTS: Best-actor Oscar for Gladiator (2000); best-actor Oscar nominations for The Insider (1999), A Beautiful Mind (2001). WHAT HE SAID THEN: “I just get on a plane and go to work, but I also know where I come from.”

Photo: Photograph by Sam Jones.

ZACH GALIFIANAKIS, NOVEMBER 2010

BREAKTHROUGH ROLE: Alan in The Hangover.CAREER HIGHLIGHTS:Birdman, Up in the Air. Two prime-time Emmys for Between Two Ferns with Zach Galifianakis.WHAT HE SAID THEN: “I didn’t know anyone in L.A. [I did] lots of shows in churches and stores, bowling alleys and laundromats.”

Photo: Photograph by Sam Jones.

RYAN GOSLING, JUNE 2002

BREAKTHROUGH ROLE: Noah in The Notebook.CAREER HIGHLIGHTS:The Big Short, Blue Valentine. Best-actor Oscar nomination for Half Nelson (2006). WHAT HE SAID THEN: “[Growing up,] I never left the house. . . . I just went to the movie store. I basically watched the whole store.”

Photo: Photograph by Paul Jasmin.

MICHAEL FASSBENDER, FEBRUARY 2010

BREAKTHROUGH ROLE: Lieutenant Archie Hicox in Inglourious Basterds.CAREER HIGHLIGHTS:Shame. Oscar-nominated for Steve Jobs (2015), 12 Years a Slave (2013). WHAT HE SAID THEN: On working with Andrea Arnold for Cannes Grand Jury Prize-winning Fish Tank: “I told her it’s totally different from how I usually work. But who’s to say that my way is the right way?”

Photo: Photograph by Sam Jones.

LEONARDO DICAPRIO, MARCH 1995

BREAKTHROUGH ROLE: Toby in This Boy’s Life.CAREER HIGHLIGHTS: Jack in Titanic—at age 23. Oscar-nominated for The Revenant (2015), The Wolf of Wall Street (2013), Blood Diamond (2006), The Aviator (2004), What’s Eating Gilbert Grape (1993). WHAT HE SAID THEN: “I can’t stand movies about reality that don’t deal with that reality.”

Photograph by Michael Roberts.

CHANNING TATUM, APRIL 2009

BREAKTHROUGH ROLE: Tyler Gage in Step Up.CAREER HIGHLIGHTS:Foxcatcher, Magic Mike, 21 and 22 Jump Street.WHAT HE SAID THEN: “I got introduced to the whole modeling thing and then I did a Pepsi commercial. That was a lot more interesting to me than just standing in front of a camera with some clothes on.”

Photograph by Norman Jean Roy.

VIN DIESEL, APRIL 1999

BREAKTHROUGH ROLE: Private Caparzo in Saving Private Ryan.CAREER HIGHLIGHTS:Fast & Furious franchise. WHAT HE SAID THEN: “When I was seven ... buddies and I vandalized this theater. The lady caught us and said, ‘Come here every day after school. I’ll pay you $20 a week.’ ”

Photograph by Mike Ruiz.

RUSSELL CROWE, SEPTEMBER 1997

BREAKTHROUGH ROLE: Bud White in L.A. Confidential.CAREER HIGHLIGHTS: Best-actor Oscar for Gladiator (2000); best-actor Oscar nominations for The Insider (1999), A Beautiful Mind (2001). WHAT HE SAID THEN: “I just get on a plane and go to work, but I also know where I come from.”

DANIEL CRAIG, MAY 2005

BREAKTHROUGH ROLE: Connor Rooney in Road to Perdition.CAREER HIGHLIGHTS: Four James Bond films; The Girl with the Dragon Tattoo.WHAT HE SAID THEN: “[I’ve been] trying to be ... picky [with roles] because I’m a snob, and I don’t like doing shit.”

Photograph by Julian Broad.

TERRENCE HOWARD, JULY 2005

BREAKTHROUGH ROLE: DJay in Hustle & Flow.CAREER HIGHLIGHTS:Crash, Empire. Best-actor Oscar nomination for Hustle & Flow (2005). WHAT HE SAID THEN: “50 [Cent] came up to me and was like, ‘I had a dream, and I always have dreams that come true, and you were so huge.... You ‘bout to be huge!’”

Photograph by Amanda de Cadenet.

BEN AFFLECK, MARCH 1997

BREAKTHROUGH ROLE: Holden McNeil in Chasing Amy.CAREER HIGHLIGHTS: Best-picture Oscar for Argo (2012); best-original-screenplay Oscar for Good Will Hunting (1997). WHAT HE SAID THEN: He co-wrote Good Will Hunting “because by the time Matt Damon and I used to get a script, 18 other people had to have passed on it.”

Photograph by Eika Aoshima.

JARED LETO, FEBRUARY 1997

BREAKTHROUGH ROLE: Jordan Catalano in My So-Called Life.CAREER HIGHLIGHTS:Requiem for a Dream, Fight Club. Best-supporting-actor Oscar for Dallas Buyers Club (2013). WHAT HE SAID THEN: “I’m so over [partying]. Living in New York, I got all that out of my system.”

Photograph by Stephen Danelian.

TOM HARDY, JULY 2010

BREAKTHROUGH ROLE: Charles Bronson/Michael Peterson in Bronson.CAREER HIGHLIGHTS:Locke, The Dark Knight Rises, Mad Max: Fury Road. Best-supporting-actor Oscar nomination for The Revenant (2015). WHAT HE SAID THEN: “I’m still very hungry. I still have a lot to prove.”

Photograph by Jason Bell.

ZACH GALIFIANAKIS, NOVEMBER 2010

BREAKTHROUGH ROLE: Alan in The Hangover.CAREER HIGHLIGHTS:Birdman, Up in the Air. Two prime-time Emmys for Between Two Ferns with Zach Galifianakis.WHAT HE SAID THEN: “I didn’t know anyone in L.A. [I did] lots of shows in churches and stores, bowling alleys and laundromats.”

Photograph by Sam Jones.

RYAN GOSLING, JUNE 2002

BREAKTHROUGH ROLE: Noah in The Notebook.CAREER HIGHLIGHTS:The Big Short, Blue Valentine. Best-actor Oscar nomination for Half Nelson (2006). WHAT HE SAID THEN: “[Growing up,] I never left the house. . . . I just went to the movie store. I basically watched the whole store.”

Photograph by Paul Jasmin.

MICHAEL FASSBENDER, FEBRUARY 2010

BREAKTHROUGH ROLE: Lieutenant Archie Hicox in Inglourious Basterds.CAREER HIGHLIGHTS:Shame. Oscar-nominated for Steve Jobs (2015), 12 Years a Slave (2013). WHAT HE SAID THEN: On working with Andrea Arnold for Cannes Grand Jury Prize-winning Fish Tank: “I told her it’s totally different from how I usually work. But who’s to say that my way is the right way?”